A Challenger
by AnotherMember
Summary: AU: Chloe has become Lex's closest friend, but Lex isn't sure if friendship is really enough. Things become even more complex when an old rival of Lex's comes into the fold.
1. Chapter 1

_It was an average day in Metropolis and a less than interesting day at Luthor Corp as Lex Luthor poured over fundraiser details in his luxurious, top floor, private office. Most saw him as a man who prospered in the solitude but the reality was he was a lonely man with trust issues, to put it politely._

 _But his average, oh so boring day was about to be interrupted by his favorite smiling face. She, being the only girl he could trust, barged into his office without any hesitation or even the announcement of a knock, something not many would even consider to try._

 **Chloe:** Hey. I brought you a scone.

 **Lex:** How was the date?

 **Chloe:** The biggest word he probably used was "touchdown" and he came in his high school letterman's jacket. I mean it might have just been a coffee date but _this_ takes effort.

 **Lex:** Well I think you look beautiful.

 **Chloe:** Thank you.

 **Chloe:** So what have you been up to?

 **Lex:** I was just preparing for a meeting with a representative from Queen Industries. We are cohosting a fundraiser next month and are just going to iron out the details.

 **Chloe:** Oh that's nice. What's the fundraiser for?

 **Lex:** A women's literacy program cofounded by my mother and the departed Mrs. Laura Queen.

 **Chloe:** That's incredible. You know what I say, women are the future and the better educated we are, the better the world can be.

 **Chloe:** I'm surprised though. From what I heard though, her son Oliver Queen is a total playboy, slacker. But then again, he has been able to run his company pretty great, so maybe not a complete slacker. But still probably-

 **Lex:** You planning on breathing anytime soon.

 **Chloe:** Sorry you know me. Once I get started on something I can't stop.

 **Lex:** I find it charming.

 **Chloe:** That would make you a party of one.

 **Chloe:** Well I just came by to drop off the scone so I'll just take my dud date coffee and get out of your hair.

 **Lex:** No matter how many times you say that, it doesn't get funnier.

 **Chloe:** Says you. Talk to you later.

 **Lex:** Can't wait.

 ** _Lex's Thoughts:_** _You truly are my favorite part of the day._

 _Chloe bid Lex farewell and began to make her way to the elevator. As she turned the final corner though she bumped into someone and spilled her coffee._

 **Chloe:** I am so sorry.

 **Oliver:** No worries. Lucky for us your coffee was cold.

 **Chloe:** But I completely ruined your suit and all your papers. I just... I am so sorry.

 **Oliver:** Don't worry. Everything is backed up online and you know maybe the spilled coffee will give me a leg up. You know make me stand out a bit.

 **Chloe:** You don't need the coffee for that.

 **Chloe:** And I can't believe I just said that out loud.

 **Oliver:** Don't take it back. A compliment from a beautiful girl is always welcomed.

 _Chloe couldn't help but blush and smile at the handsome man complimenting her._

 **Oliver:** Not to mention that smile.

 **Chloe:** Well um, there has to be something I can do.

 **Oliver:** You know if you really want to make it up to me you could always let me take you out for a proper, warm cup of coffee.

 **Chloe:** Um...

 _Though it really shouldn't have, his comment caught Chloe off guard; she could feel the shock reach her face._

 ** _Chloe's Thought:_** _Great as if I wasn't blushing enough._

 **Oliver:** Or you could always direct me towards Lex Luthor's office.

 **Chloe:** I will show you the way.

 **Chloe:** I'm Chloe by the way. Chloe Sullivan.

 **Oliver:** Nice to meet you Chloe.

 **Oliver:** I'm Oliver -

 **Chloe:** As in Oliver Queen.

 _When they reached the marked door for Lex's office Oliver pushed the door open with his back._

 **Oliver:** You beat me to the clincher. Where's the fun in that?

 **Lex:** Chloe, did you forget something?

 **Chloe:** Um, no. I was just showing Mr. Queen to your office.

 **Oliver:** Mr. Queen, huh? Maybe I should have held off the introductions a bit longer.

 **Oliver:** Lex. How've you been?

 **Lex:** Oliver. Do you always attend meetings late and wearing your coffee?

 **Oliver:** I got distracted.

 _Oliver couldn't help but look at Chloe and Chloe couldn't help but notice, and more than slightly enjoy the attention._

 **Chloe:** Don't blame him; it's my fault. I totally fumbled and-

 **Lex:** Chloe breathe.

 **Chloe:** And that makes two in like 15 minutes.

 _Oliver looked at her quizzical._

 **Chloe:** I have a bit of a habit of not being able to stop talking, at least when it comes to certain topics. And I know, it's annoying.

 **Oliver:** Won't hear any complaining from me. In fact I'm flattered that our first meeting got you so flustered.

 _Chloe tried to respond but the way he said, or more accurately because he was the one to say it all she could was once again smile._

 ** _Chloe's Thought:_** _Seriously blushing, again. Get it together Chlo._

 **Oliver:** Leaving intelligent girls speechless also helps with the ego boost.

 **Chloe:** From what I've gathered so far, you don't need much help in the ego department.

 _Chloe finally was able to show her more common, coy smile and this time cause Oliver to be the one with the nerve blush and a shy grin. Between the continuous banter, not to mention the flirting, the two couldn't help but to become caught with their eyes locked, in an interment moment._

 _Sadly they weren't truly alone and their moment was quickly broken by a 'through clearing' by an differently irritated Lex._

 **Lex:** Well if that is all, Oliver and I should probably start our meeting.

 **Chloe:** Right. I'll get out of your guys' way. Talk to later Lex.

 **Oliver:** What about me?

 **Chloe:** I guess we'll see what fate has in store.

 **Chloe:** Mr. Queen.

 **Oliver:** Miss Sullivan.

 _Chloe made her way out the office, leaving Lex and Oliver to their duties but not without a final remark._

 **Oliver:** Interesting girl you got there Lex.


	2. Chapter 2

_It was a new day and Chloe had another early start in the bullpen of the Daily Planet. It was only 2 in the afternoon but Chloe was already on her third cup of coffee. She was on her way out to grab lunch, and the another cup of the early mentioned beverage from a cafe across the street when she bumped into a recently familiar yet completely unexpected face._

 **Oliver:** Miss Sullivan! Nice to see you again.

 **Chloe:** Mr. Queen. What are you doing here?

 **Oliver:** I was going to go talk to the City Editor about assigning a journalist for the Fundraiser next month. So you work here?

 **Chloe:** Uh, yeah. I just -

 **Oliver:** You want the story?

 **Chloe:** What?

 **Oliver:** Will you take the story and cover the Fundraiser?

 **Chloe:** Um, sure but -

 **Oliver:** Great! Let me see now, here. Call me and we can set up a meeting.

 **Chloe:** You mean your assistant?

 **Oliver:** No, I mean me. That's my personal number.

 **Oliver:** You know actually I have time tonight if you're not busy.

 **Chloe:** I'm not, but -

 **Oliver:** Perfect. Then how about we meet up at let's say 6. My address is on the bottom of the card.

 **Chloe:** Wait. What about -

 **Oliver:** And can you handle informing the editor for me, thanks. See you tonight.

 _Before Chloe could respond, Oliver took Chloe's hand to place a gentle kiss and made his abrupt exit back up the stairs, out of the Daily Planet. Chloe was left standing alone both stunned and confused by her second encounter with the renowned billionaire CEO. She quickly realized that she could do nothing but accept his offer, but that still didn't stop her from questioning._

 **Chloe:** What just happened?

* * *

 _At Queen's Clocktower Penthouse. It had been merely 30 minutes and already Chloe had dove far past the deep end of spitfire question after question, always prepared with a follow-up. This may have been an unexpected assignment but that didn't change the fact that a one-on-one with Oliver Queen was a golden opportunity for this junior reporter._

 **Oliver:** Wasn't this supposed to be about the fundraiser?

 **Chloe:** An interview with Oliver Queen isn't something that always falls into your lap, a good journalist gets the most possible out of every opportunity.

 **Oliver:** Interesting way of putting it.

 **Chloe:** So where was I. Oh right, what can you say about the partnership between Luthor Corp and Queen Industries?

 **Oliver:** What about it?

 **Chloe:** How does working with Lex Luthor affect the friction relationship between the two companies? Any chance of future endeavors together?

 **Oliver:** No.

 **Chloe:** Well that was blunt. Care to elaborate?

 **Oliver:** I don't see this as a project with Luthor. This is me and the son of my mother's friend working towards the same important cause.

 **Chloe:** Would it be correct to presume that the collaboration isn't going well then?

 **Oliver:** I would never jeopardize this event. Our feelings for each other doesn't change how important this fundraiser was to my mom, she truly believed in this cause. I think the value it held with our individual moms makes it easier to ignore anything that would normally cause tension.

 **Chloe:** That's good to hear.

 **Oliver:** Do you mind if we take a bit of a breather? I feel like I've just been grilled by an entire press conference worth of reporters.

 **Chloe:** Since I see that as a compliment to my journalism skills I guess it's okay.

 **Oliver:** Great. Would you mind a cup of evening coffee?

 **Chloe:** Oh, now you're reading my mind.

 **Oliver:** You're easier to read than you think Miss Sullivan. But then again I do have a bit of an invested interest.

 **Chloe:** Meaning?

 **Oliver:** That you will find out in due time, I hope.

* * *

 _Once the coffee was prepared Oliver joined Chloe on the balcony with the warm beverages. When he reached outside he saw Chloe more than just admiring his view, she looked like she was truly trying to embrace what made his corner of world different from the rest, it was admirable to watch. The blonde joined the other the reporter and handed her the freshly brewed cup. Chloe's emerald eyes nearly lit up as she took in the robust aroma._

 **Chloe:** It smells amazing, thanks.

 **Oliver:** No problem.

 **Oliver:** You know, those last couple questions reminded me I wanted to ask you about something.

 **Chloe:** Usually I'd object but since you're such a great last minute assignment and you made me coffee, I'll consider answering.

 **Oliver:** You and Lex.

 **Chloe:** Are just friends.

 **Oliver:** Still worth remarking on.

 **Chloe:** Look I know all about the Luthor villainy, trust me. I use to basically be the Down With Luthor Club president.

 **Oliver:** And now you're sharing private face time in the beast's cave.

 **Chloe:** You know your tone is pretty inappropriate considering we just met.

 **Oliver:** Sorry I just... sorry

 **Oliver:** So what changed?

 **Chloe:** You remember a few years ago when Lionel was convicted for murdering his parents.

 **Oliver:** Highlight of 2004.

 **Chloe:** Well I was the lead witness and long story short in the months leading up to the trial Lex was the only person I could talk to, other than my dad and uncle.

 **Chloe:** I guess between being the object of obsessive protection and the time I got to actually get to know Lex on a more human level the more I was willing to, I guess accept about him.

 **Chloe:** Anyways now we're friends.

 **Oliver:** You don't seem like the kind of person to be blind enough to trust him.

 **Chloe:** I never said that I did.

 **Oliver:** But I thought.

 **Chloe:** Just because we're friends doesn't mean I trust him. Trust means being able to let your guard down and be the truest version of yourself.

 **Oliver:** Interesting thought.

 _There was a moment of silence as the two sipped their coffees and just enjoyed the sight from the extravagant penthouse and in Oliver's case the present of his beautiful guest. But the quiet didn't last long for the boy billionaire was still curious and desired to learn as much about Chloe Sullivan as possible._

 **Oliver:** So is there anyone?

 **Chloe:** Anyone who what?

 **Oliver:** Whom you trust? Who knows your truest self?

 **Chloe:** No, not since I left Smallville. Definitely, no one who's ever really understood me.

 **Oliver:** Meaning?

 **Chloe:** I don't think there has ever really been anyone who I felt got me. I always hope that someone would see me, but they never did and I've accepted.

 ** _Chloe's Thought:_** _Why did I just tell him that, and so easily._

 **Oliver:** Maybe it's time for that to change.

 **Chloe:** What was that?

 **Oliver:** I was just saying that's a shame.


End file.
